Trifluoroacetic acid → 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-[2-(1H-imidazol-1-yl)ethoxy]ethanone

Beteiligte Stoffe

Reaktionsschritte

Add trifluoroacetic acid (2 mL) dropwise to a solution of tert-butyl 2-(2-imidazol-1-ylethoxy)acetate (0.375 g; 1.0 equiv; 1.66 mmoles) in dichloromethane (10 mL). Stir at room temperature for 4 hours and then concentrate the mixture. Redissolve the remaining residue in dimethylformamide (5 mL) and add diisopropylethylamine (1.45 mL; 5 equiv; 8.31 mmoles) followed by N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.44 g; 1.0 equiv; 1.65 mmoles). Add O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.69 g; 1.1 equiv; 1.81 mmoles) and stir at room temperature for 16 hours. Pour the reaction mixture into saturated aqueous sodium bicarbonate solution (200 mL) and extract with dichloromethane (2×200 mL). Wash the combined organic extracts with saturated aqueous sodium bicarbonate solution (100 mL), dry over sodium sulfate, filter, and concentrate to give the crude product. Purify this residue by column chromatography (0 to 20% methanol in dichloromethane) to afford 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-[2-(1H-imidazol-1-yl)ethoxy]ethanone (0.152 g; 22%) as a light brown solid: MS (m/z): 419(M+1).

Herkunft & Nachweise